Category Archives: Key West Walkabouts

Here’s the second part of the Caroline Street Walkabout. Click on the link to open another window to youtube. Let it play in the background as you read on. Woman Goin’ Crazy on Caroline Street.

After you finish your coffee at the Coffee Plantation, walk less than a block more you’ll come to the “heart” of the old “Caroline Street”… the part Jimmy Buffett’s sings about.

Look over to the left as you cross over William Street and you will see down to the seaport. That’s where Schooner Wharf Bar is. Maybe you will want to stop in there for a little “refreshment” on your way back.

After you cross William, B.O.’s Fish Wagon is right there on the left… the corner or Caroline and William. Whenever I tell someone about B.O.’s they always make a funny face and ask why in the world would anyone name a place to eat, “B. O.’s?”… Pppp-Uuuuu. Well, the real reason is that the owner’s name is Buddy Owen (or maybe it’s Owens). And the “Fish Wagon” part comes from the old mobile food truck… the fishwagon… inside and where the food is prepared. The fishwagon hasn’t moved in years.

B.O.’s is a funky place. Don’t expect any fancy tablecloths or even silverware. You get an almost outdoor setting… just sitting under umbrellas… garden furniture and picnic tables. There are always two or three… or more of Key West’s “Gypsy Chickens” wandering around looking for a morsel that makes it’s way to the cement floor.

B.O.’s Fishwagon

This old, derelect truck at B.O.’s is probably worth a fortune… but it just sits there collecting stickies.

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Don’t let the name or any of the other stuff stop you from going in to have a bite to eat. The fish sandwiches are among the very best on an island that serves fish sandwiches everywhere. And the homemade black beans & rice are also mmmmm-mmmmm good. You can get beer and wine at B.O.’s but no frozen concoctions to help you hang on.

Right across the street from B.O.’s is the “Red Doors’. Today, the Red Doors has a boutique in the lower level. But back in the times Jimmy sings about, the Red Doors was one of the roughest, toughest, and rowdiest saloons anywhere. The upstairs area was a brothel.

The Red Doors… with a history of booze, broads, gambling and fighting. Fun in Key West.

According to Tiffany, who also does a blog about her travels, her Great-Great-Grandpa owned and managed the Red Doors back in the 1920s. It was called the “Bucket of Blood” back then. She says it was called that “because of all the stabbings, violence and occasional ‘quiet’ murder.” (I couldn’t confirm Tiffany’s last name, so I’ll let you be the detective. Link to Tiffany’s Blog)

I always wonder what goes on upstairs above the “Bucket of Blood” these days. One time I wandered into the boutique and asked the attendant about the upstairs. She only gave me some vague non-answer. I don’t know if she was trying to add to the mystique of the place, or just didn’t want to say. So, I still wonder if there is any “business” of the old days.

A couple of “doors” down is Pepe’s Cafe… which claims to be the oldest eating establishment in the Florida Keys. From the looks of the building, I’m sure it is very old. In most places of the world, I would never consider eating in any place looking that old and rundown. But this is Key West.

Pepe’s Café… est. 1909. No doubt it’s that old.

Pepe’s used to be a great place for breakfast. I say “used to be” because these days, you may not be able to get a table. There’s an inside area and a covered patio area, but the visitors have discovered Pepe’s. You’ll have to wait at the bar on most mornings before you can get a table.

Sometimes the wait at the bar isn’t so bad because they do make good Bloody Marys… but these days I’m not willing to wait very long… especially when the Schooner Wharf Bar is close, and they have good breakfast too. BUT… if you do get a seat at Pepe’s the food will be good. Over time I’ve had eggs (build your own breakfast), French toast, and pancakes and all were excellent.

Oh… and don’t forget the Mimosas or screwdrivers made with fresh squeezed orange juice. Both are mmmmm-mmmmm good. They also claim to have “fresh squeezed Margaritas,” but I’m not sure what that is and never had one.

The last block of Caroline Street has the “Flagler Station Railway Historeum. The name Flagler probably doesn’t mean anything to most of you. But without Henry Flagler, much of Florida and Key West wouldn’t be what it is today.

Flagler Station – A significant part of the history of Florida and Key West

Flagler became partners with John D. Rockefeller… yeah, that Rockefeller. I won’t try to tell you the whole story here… you can google it… but the essence is: Flagler was rich. He built the railway all along the east coast of Florida down to Biscayne Bay in Miami.

Then when Flagler was 75 years old, he built the railway that connected the Mainland (Homestead) to Key West. It was started in 1905 and was finished in January 1912. At the time, it was the only way to get to Key West other than by ship. The Overseas Highway didn’t come along till much later.

The railway ran until the 1935 Labor Day hurricane took out sections of the railroad. You can still see sections of it today as you drive the Overseas Highway. The museum has a little house and a train car that shows the railway history with artifacts and videos. It only costs three bucks and is worth the time.

My next walkabout (in a few days) will be to the sunset celebration at Mallory Square. It’s one of the things that puts the character and characters of Bone Island on full display.

It seems the last few days I’ve been obsessing about Key West. OK… maybe I’m always obsessing about the place, but the last few days especially so. Anytime I’m overdue a trip to The Rock I begin obsessing.

To give me a little bit of a “fix,” I decided to write about Caroline Street. A few posts back, “Dear Ben,” I wrote to Ben Gentry about the Jimmy Buffett song, “Woman Going Crazy on Caroline Street.” The song is about Caroline Street in Key West. The lyrics tell the tale of the street back when fishin’ and shrimpin’ were king in Key West… back when it was rough and rowdy.

Today Caroline street is different. So I thought I would take you on a “walkabout” down the street… if only in my mind. I’m including pics so you will get the feel.

Starting at the corner of Duval and Caroline there’s the Bull & Whistle. It’s one of my favorite bars to stop into and have a frozen concoction to help me hang on. “The Bull” is the downstairs area. Starting about noon and going well into the night they have some kind of live entertainment. If you sit by one of the open windows right on Duval, there’s plenty of entertainment out there doing the “Duval Crawl.”

Check out the roof top garden. It will be an eye opener

The second floor is the Whistle. I can’t say much about it because I haven’t spent much time there. The Whistle does have a balcony all around so you can watch the Duval Crawl from there. I suspect it’s a great place to watch any of the hundreds of doo-dah parades down Duval.

The third floor, actually the roof of the Bull & Whistle, is… well… I’ll leave that for you to discover for yourself. Go there on a cool afternoon (in Key West that means the low 80s) or one weekend in the evening after the sun sets. I promise you it will be an eye-opener for you.

We start our walkabout heading toward the old seaport… away from Mallory Square and the Cruise port. By the time you are one short block away from Duval, all the craziness is left behind. Caroline becomes a sedate, almost stately neighborhood.

Tall mature trees and palms line both sides of the road and almost form a canopy covering the street in some places. The houses are mostly two-story with a mix of colors and surrounded by white picket fences. Most have a wide veranda around the bottom floor and a balcony around the top floor.

Many of the houses have been divided into small apartments. Most of those are little more than the size an efficiency in any other town… around 300 square feet. Each one costing way more a month than the original cost to build the entire house. Such is the cost of living there.

Sedate and stately just one block from Duval

If these houses could tell stories, I wonder what they would say.

Walk a little more down toward the seaport and a bit after you pass Elisabeth Street, you will come to my favorite little coffee house in all of Cayo Hueso… The Coffee Plantation at 713 Caroline St.

The Coffee Plantation is half coffee house, half art store. I found the place because an artist I know once lived near there. I always stopped in hoping to see some of the artists work or to maybe run into the artist. But that was not to be… the artist had moved before I found the Coffee Plantation.

Have a “cupa” and enjoy the “mullet wrap.”

Just the same, I still go to the Coffee Plantation every time I’m in Key West. Besides good coffee, you can have a seat in one of the couches inside or around the outside porch. Inside you’ll see some magnificent local art. I always want to take some home… until I see the prices.

So I just sit there and sip my coffee and maybe read the local newspaper… the “Key West Citizen.” Some call that paper the “mullet wrap.” Like most newspapers, it has fallen on hard times lately, but it’s always an interesting read. While sitting there, inside or outside, it’s more than likely that you will strike up a conversation with another of the patrons. It seems like most people are friendly there.